abstract
The biomimetic oxidation of caffeine with hydrogen peroxide using metalloporphyrins as catalysts, which are known to be good biomimetic models of cytochrome P450 enzymes, is investigated. The two manganese porphyrins tested, chloro[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]manganese(III), [Mn(TDCPP)Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(III), [Mn(TPEPP)Cl], afford high conversions of caffeine for all substrate/catalyst molar ratios. Selectivity was found to be dependent on the catalyst employed, and a new spiro racemic compound is described and fully characterized in the solid state from X-ray diffraction studies. (C) 2011 Elsevier Ltd. All rights reserved.
keywords
EPOXIDATION REACTIONS; PORPHYRIN COMPLEXES; MN(III) PORPHYRINS; MASS-SPECTROMETRY; METABOLISM; HISTORY
subject category
Chemistry
authors
Neves, CMB; Simoes, MMQ; Santos, ICMS; Domingues, FMJ; Neves, MGPMS; Paz, FAA; Silva, AMS; Cavaleiro, JAS
our authors
Filipe Alexandre Almeida Paz
Principal Researcher
Isabel Cristina Maia da Silva Santos Vieira
Junior Researcheracknowledgements
Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT/FEDER) for funding QOPNA and CICECO and for specific funding towards the purchase of the single-crystal X-ray diffractometer. Authors acknowledge the Portuguese National NMR Network (RNRMN), supported with funds from FCT.